A Fresh Look at the Staudinger Reaction on Azido Esters: Formation of 2H-1,2,3-Triazol-4-ols from α-Azido Esters Using Trialkyl Phosphines
Scott D. Taylor* and Chuda Raj Lohani
*Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, Ontario Canada, N2L 3G1, Email: s5tayloruwaterloo.ca
S. D. Taylor, C. R. Lohani, Org. Lett., 2016, 18, 4412-4415.
DOI: 10.1021/acs.orglett.6b02204 (free Supporting Information)
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Phenyl esters of α-azido acids react with trialkylphosphines in THF/H2O to give 5-substituted 2H-1,2,3-triazol-4-ols in very good yields, whereas their reaction with PPh3 provides amino esters as the major product and no triazoles.
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